The present invention relates to novel compositions and processes using 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone to alter, modify, augment, or enhance the aroma of detergents or impart aroma to detergents.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) fragrances to (or in) detergents. These substances are used to diminish the use of natural materials, some of which may be in short supply, and to provide more uniform properties in the finished product.
Floral, fruity, musky and tobacco aromas with rose notes and hay-like and menthane-like undertones are desirable in several types of perfume compositions, perfumed articles and colognes.
3-Hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone, having the structure: ##STR2## has heretofore been indicated by Ayyar, Cookson and Kagi, J. Chem. Soc., Perkin I, 1727 (1975) (Title: "Synthesis of .DELTA.-Damascone [trans-1-(2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one] and beta-Damascenone [trans-1-(2,6,6-trimethylcyclohexa-1,3-dienyl) but-2-en-1-one]") to be useful as an intermediate in preparing "Damascenone" the "beta" isomer of which has the structure: ##STR3## Ayyar, Cookson and Kagi do not, however, teach the usefulness of 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone for its organoleptic properties.
Schulte-Elte, U.K. Patent specification No. 1,391,736 discloses and claims a genus of compounds which include 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone and uses of their organoleptic properties but does not specifically teach any specific cyclohexadiene compounds per se or their uses for their organoleptic properties. Thus, U.K. Patent specification No. 1,391,736 states:
"The compounds to which the invention relates have the formula: ##STR4## wherein: X represents the group: ##STR5## R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 may be the same or different, and each represents a hydrogen atom or a lower alkyl group having from 1 to 6 carbon atoms; and the ring is saturated or contains one edocyclic double bond in positions 1, 2, 3 or 4, or an exocyclic double bond in position 2, or two conjugated double bonds in positions 1 and 3 . . . PA1 The new compounds of formula (I) include the following specific examples: PA1 2,6,6-trimethyl-1-(1,3-dioxo-but-1-yl)-cyclohex-1-ene; PA1 2-methylene-6,6-dimethyl-1-(1,3-dioxo-but-1-yl)-cyclohexane; PA1 2,6,6-trimethyl-1-(3-hydroxy-butan-1-oyl)-cyclohex-1-ene; PA1 2,6,6-trimethyl-1-(3-hydroxy-butan-1oyl)-cyclohex-2-ene; PA1 2,6,6-trimethyl-1-(2-methyl-1,3-dioxo-but-1-yl)-cyclohex-1-ene; PA1 2,6,6-trimethyl-1-(2-methyl-1,3-dioxo-but-1-yl)-cyclohex-2-ene; PA1 2-methylene-6,6-dimethyl-1-(2-methyl-1,3-dioxo-but-1-yl)-cyclohexane; PA1 2,6,6-trimethyl-1-(2-methyl-3-hydroxy-butan-1-oyl)-cyclohex-2-ene; PA1 2-methylene-6,6-dimethyl-1-(2-methyl-3-hydroxy-butan-1-oyl)-cyclohexane; PA1 2,6,6-trimethyl-1-(2-methyl-1,3-dihydroxy-but-1-yl)-cyclohex-2-ene; PA1 2,6,6-trimethyl-1-(2-methyl-1,3-dihydroxy-but-1-yl)-cyclohex-1-ene; PA1 2,6,6-trimethyl-1-(1,3-dioxo-but-1-yl)-cyclohexane; PA1 2,6,6-trimethyl-1-(1,3-dihydroxy-but-1-yl)-cyclohexane; PA1 2,6,6-trimethyl-1-(1,3-dihydroxy-but-1-yl)-cyclohex-2-ene; and PA1 2,6,6-trimethyl-1-(1,3-dihydroxy-but-1-yl)-cyclohex-1-ene."
None of the exemplified compounds of U.K. Patent specification No. 1,391,736 has a chemical structure which can be considered by one having ordinary skill in the art to be even remotely similar to 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone.
A sulfur analogue of 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone, which sulfur analogue has the structure: ##STR6## is disclosed as having useful organoleptic properties in U.S. Pat. No. 3,979,422. The organoleptic properties of the compound having the structure: ##STR7## are different in kind from the organoleptic properties of 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone having the structure: ##STR8## and, the properties of 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone are unexpectedly and unobviously advantageous insofar as the taste and aroma nuances are concerned and further insofar as the intensity and lasting power is concerned.